​Sail history's sights aboard part of it.​ See the Maine Coast from one of the sights.

Family Business!

I'm Captain Daniel Bennett owner & operator. My daughter, Raya, has crewed aboard for 7 of her 10 years. My wife, Amanda, helps with shoreside logistics and support as well as our early crew training program for our son, Silas, who at 3 1/2 is just starting to come out as effective crew.

Together, we run a tight ship and its business, a bit of a homestead and a happy family. Amanda also works in the food and wine industries, as well as making jewelry, awesome food and great communications happen.

We appreciate your patronage by sailing with us and your online support by sharing your enjoyment. ​

Thank You and Welcome!

Flexible, custom sailing tours

Choose your own Adventure

Book a sail on Bufflehead because flexible scheduling allows us to offer a quick highlight to your trip, or a full day of sights, memories and meals. It also makes planning your vacation easier. We sail when you want, for how long you want, even our motto is "Do What You Want." You're welcome to bring anything you like, or we can cater you.

My mission is to see that,​in the time and tides we share aboard,​I'll find you the best of what the day offers​and suits you most.

​​Our family offers Maine sailing charters of the beautiful coast aboard a classic wooden boat; custom daysail charters for up to six people on a safe and nimble 32' gaff sloop. Sunset sails, lobsterbakes,island picnicsand night sails are also options.

​You can bring whatever food or drinks you like, or we can cater local delights to complete your Maine experience, and let us support or spoil you as we're known for doing. Special events are our specialty, as well as making the ordinary extraordinary.

We run our boat to create memorable custom experiencesfor our guests, 1 - 6 people at a time,​doing what YOU want.

Bufflehead sails the area so much that people often recognize us & call out with greetings from the shore.

​We tour Penobscot Bay from Rockland's historic working harbor to see islands, lighthouses, lobstering, wildlife and our local fleet of historic, working sailboats.

Imagine sailing along the rugged scenery of Maine's coast aboard Bufflehead: inhaling the tasty light spice of salt in the clean ocean air, hearing the bow splash as we smoothly cruise along the glistening water, waving to passing schooners, spotting wildlife, seeing lighthouses and exploring islands.

Every day is different and the light is always changing. Don't miss out on this authentic Maine sailing experience. Come sail and share the beauty and interest as we explore among the islands of Maine.